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Jack is a weirdo. A wonderful weirdo, but a dues-paying, card-carrying weirdo all the same. If you had to pick out which one was the dope-holding Grateful Dead roadie in a police line-up, Jack is your guy. Maybe that’s what made him such a great parole officer. His collar-crowding Scotch-white hair, beaded hippie vests and standard issue al-Qaeda–brand facial growth made him a beacon for other weirdoes. Like me.

“I brought you something,” he said to me many summers ago. “For the road ahead.”

I took the paper bag from him and turned it over in my hands. Its white waxy surface reminded me of the back of Jack’s hands — hands I had clasped in greeting may times. But today was different. Today was all about the goodbyes. I opened the bag and peeked inside.

“A book. Wow, Jack — that’s great.” And I meant it. Finding the right gift for me is about as hard as picking out a wino’s favourite flavour of swish. If it comes with a title and has words inside, you’ve got me.

“Take a look.”

I pulled out the thin, blue paperback. The Little Prince by Antoine de Saint-Exupery. The glossy cover showcased a whimsical piece of children’s art. “That’s really cool, Jack. I’ll bring it with me for the kids at our next private family visit. Thanks.”

I scanned the cover again, this time more carefully. After 25 years as a community parole officer, today was Jack’s last day as a shill for the man. Tomorrow he was retiring. And this trip back inside the prison was just to see me — and give me this copy of an obviously Grade 3 reader. Apparently I was missing something. I quick-thumbed the 30-page storybook, hawking deep into its crevices. No handcuff key, no half a hacksaw blade. I still didn’t get it.

“Don’t worry. Just read it. You’ll figure it out. And keep an eye on the fox.” And with that, the only parole officer I ever truly respected was gone. But I thought about him again this week, while weeding my bookshelf to make space for new arrivals. I blew the dust from Jack’s decade-old gift and coughed a small smile into the lingering cloud. Keep an eye on the fox. It took a few years but I finally figured out what wacky Jack meant — and that the fox he was talking about was the same one he had given the book to.

One of the things that the above-ground crew doesn’t get about the underworld is how the same guy who can put a gun in a bank teller’s face — or a bullet in someone’s eye — can also soothe a colicky baby to sleep. Water-collar wisdom says that guys like that are just plain wrong — sociopaths, for whom the only fix is a bullet — or maybe something slower. But while that philosophy might sell a lot of cable-news ads (and buy a lot of votes), the truth is far less complicated.

“I’m going to die here,” said Stamper. In his hands was the three-page decision sheet he had been waiting a month for. But of all the words filling both sides of the legal-sized paper, only one mattered: Denied. As in denied — after 29 years behind bars — for a transfer to minimum security. The 70-year-old con filled the room with his silence.

Scotch Bob, the half-Scottish, half-Mohawk, fully disillusioned was the first to break the vacuum. “Can I have your new Stones CD when you go?” Normally, Stamper would have countered with a barb that involved rusty piano wire, adult incontinence products (used), and Kraft barbecue sauce. But not today.

“The thing is …” said Kaukaughe, assuming the cloak of First Nations philosopher king, “guys like us scare the shit out of them. Because we do whatever we want. So if you ain’t on a ventilator — or at least dialysis, you ain’t goin’ anywhere.”

Not exactly Chief Dan George, but it is the plain truth of the matter. What the law-fearing masses fantasize about (or amuse themselves with, via Netflix) are the same things we’re behind bars for. And regardless of the spurious twaddle prisoners clutch at to explaining themselves, the reasons we’re here hardly rely on advanced math. At any given moment we do whatever we want to.

“You become responsible, forever, for what you have tamed.” So said the fox to the little prince. Thankfully, the majority of those who bed down behind bars have tamed that which brought them here. A thousand Canadian prison guards going home safely tonight can attest to that. But I wonder if they know that the fox tamed himself, or that it did so for reasons all its own.

I.M GreNada is the pen name of a Canadian prisoner who has been serving life for murder since 1994. The people he writes about are real, but their names have been changed. You can read more about him at theincarceratedinkwell.ca.

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